Situation...
Lost all water pressure 2 days ago (on a Saturday of course!)
Reset breakers, and re-seated control box board, to no avail (left power off)
Took well-cap off and dropped in pebble and counted just ~2 seconds until spash heard (to confirm well wasn't dry)
While I'm at work my well-driller went out today (Monday) to inspect and sa when he turned all power back on, the pump kicked on and took 3+ min to fill the pressure tank
He also popped the well-cap and ensured adequate water supply and tested the pump (30 seconds to fill 5gal pail)
He then emptied the pressure tank again and re-filled it, which only took about 2 min this time, but he says that's still not good and thinks the line from well to house must be kinked or punctured, and wants to dig it up.

What are your thoughts? How long should it take to fill a 20 gal pressure tank? Could something else be wrong?

Unless it is a really short run in good diggings, that would not be my next step. If you have a leak, how do you know it is not in the well?

I would first pressure test the line from the house. Then I would lift the pipe out of the pitless up to the top of the casing. I would then cap and pressure test the drop pipe. If there are any additional checkvalves, I would remove them and test again.